Cole Simmons

In February we noticed trial-to-paid conversion had dropped from 14% to 9% with no product changes. We spent two weeks looking at the product before someone suggested checking email deliverability.

We ran a seed test across Gmail, Outlook, and Yahoo. Results:

• Gmail (personal): 94% inbox

• Gmail (custom domain): 61% inbox

• Outlook: 78% inbox

• Yahoo: 88% inbox

The custom domain Gmail number was the killer. A large chunk of our B2B users were on Google Workspace with a custom domain. Our onboarding emails, trial expiry warnings, and password resets were landing in spam for nearly 40% of them.

For me, I finish the tasks I didn t complete during the week, then try to get ahead on a few things.

And I always finish my weekend by preparing my tasks for the next week.

I know some founders completely disconnect on weekends, but I ve never really managed to do that

What about you? Do you work on weekends or completely switch off?

I tried an experiment. For 30 days, every time I caught myself making an excuse for why I wasn't doing something, I wrote it down. No editing. No judgment. Just the raw excuse.

Here are the ones that appeared most often:

• "I'll do that when I have more time."

• "I need to learn more before I start."

• "I'll wait until the product is more polished."

• "I don't want to bother people."

• "They probably won't respond anyway."

• "I'll do it tomorrow when I have more energy."

• "I should focus on building first."

Reading them back was painful. Not because any single one was unreasonable on their own, they all sound kind of sensible. But together? Together they were a wall.